Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

If you’re after a fun, slightly spooky evening in Annapolis, the Boos & Booze Haunted Pub Crawl promises a mix of ghostly tales, historic pubs, and a dash of liquid courage.

We haven’t personally taken this tour, but based on reviews and the detailed itinerary, it’s an experience that blends storytelling, local history, and a relaxed social vibe in a way that appeals to both history buffs and those just looking for a memorable night out.

Two things we really like about this tour are its well-researched stories and the cozy atmosphere of the pubs. The guide’s knowledge seems to make all the difference, transforming what could be a simple pub visit into a journey through Annapolis’ ghostly past. The 2-hour duration makes it manageable for most evenings, especially since it’s an affordable way to explore the city’s haunted side without breaking the bank.

One thing to consider is that drinks are not included in the price, so you’ll want to budget for additional purchases. Also, the tour isn’t designed for those with mobility issues, owing to the walking and standing involved. This experience suits travelers who enjoy a good ghost story, a bit of historic ambiance, and the camaraderie of a small group exploring together.

This experience made our article of The 4 Best Drinking Tours In Annapolis.

Key Points

• Authentic storytelling backed by local ghost lore and history
• Cozy pub environments that enhance the haunted vibe
• Informative guide with a friendly, approachable style
• Affordable price point for a 2-hour experience
• Not inclusive of drinks, so budget accordingly
• Ideal for those interested in history, ghost stories, and casual socializing

An Authentic Haunted Pub Crawl in Annapolis

Annapolis is known for its charming streets and historic buildings, but it also has a spooky side that many visitors find intriguing. The Boos & Booze Haunted Pub Crawl offers a chance to explore this unseen, ghostly layer of the city. This guided tour takes you through a series of historic pubs and landmarks, each with its own story of spirits and mysterious happenings.

What makes this tour stand out is its ability to combine entertainment and education. The guide is described as friendly and knowledgeable, offering thoroughly researched stories that bring the city’s haunted past to life. Authentic tales are told at each stop, from the nearly 300-year-old Middleton Tavern to the Old Annapolis Jail, and beyond.

The tour’s core appeal is its blend of history and ghostly lore. You’ll hear about the man believed to have started hauntings at St. Anne’s Parish, for example, and learn about the spirits rumored to linger at Reynolds Tavern and Rams Head Tavern. These stories aren’t just spooky — they give insight into Annapolis’ past lives, making the experience both fun and somewhat educational.

Detailed Breakdown of the Itinerary

Stop 1: Middleton Tavern
This historic tavern, nearly three centuries old, is the perfect starting point. As you step inside, you’ll hear about the spirits said to linger within its walls, including “Roland,” a mysterious ghost reportedly seen by staff. The setting’s age and ambiance lend a genuine sense of history — and haunting curiosity. The visit lasts about 20 minutes, and while the admission is free, it’s the stories that make it worthwhile.

Stop 2: 136 Dock St – Old Annapolis Jail
Here, the tour takes a darker turn. The jail’s stories of condemned prisoners and ghostly encounters are both chilling and fascinating. The tales focus on the lives of those who once awaited trials in this grim setting. Once again, it’s the local lore and the atmosphere that make this stop memorable.

Stop 3: Reynolds Tavern and 1747 Pub
A favorite among many, Reynolds Tavern is famous for legends of a resident spirit. You’re encouraged to stay on its good side while enjoying a beverage — the perfect interlude in this haunted lineup. The stories here are lively and rooted in local legend, making it a highlight for many.

Stop 4: St. Anne’s Parish
This nearly 300-year-old church survived a devastating fire in 1858, but not its ghost stories. Rumors point to a man who allegedly started the haunting, with spirits still said to lurk on the grounds. A shorter stop, around 10 minutes, but packed with history and supernatural tales.

Stop 5: Rams Head Tavern
This pub’s past is filled with tales of those who lived and worked in its walls during the 18th and 19th centuries. Guests have reported petty spirits and minor apparitions, adding a playful yet eerie dimension to the experience. The 20-minute visit is an atmospheric peek into Annapolis’ past.

Stop 6: Government House of Maryland
While not the original building, the current Government House is still steeped in history and ghostly stories. This stop offers a quieter, more reflective moment, rounding out the tour’s haunted trail.

Stop 7: Galway Bay Irish Restaurant and Pub
The final stop takes you into one of Annapolis’ most significant sites during Prohibition. You can sit down, relax, and enjoy a drink while soaking in the historic ambiance. This last stop is about 20 minutes long, giving you a chance to wind down and reflect on the evening’s tales.

The Experience You Can Expect

The entire tour lasts about 2 hours, with a friendly, engaging guide leading the way. You’ll walk from one historic pub to another, hearing ghost stories backed by local lore. The group size is capped at 25 people, which helps keep things intimate and allows for personal interaction with the guide.

Since drinks aren’t included, you may want to plan ahead or bring some cash for additional beverages. The tour starts at 6:00 pm at 22 Market Space — a convenient central meeting point — and ends there too, making it easy to continue exploring afterward.

The experience is suitable for most travelers, but it’s not recommended for those with mobility impairments, given the walking involved. Service animals are allowed, and the tour is generally accessible to most adults and older children.

Authenticity and Value

The care taken in researching and recounting local ghost stories adds a layer of authenticity many other ghost tours lack. It’s clear that the tour operators aim to blend entertainment with education, making these stories more than just ghostly tales—they’re part of Annapolis’ living history.

At $27 per person, the price is quite reasonable for this two-hour exploration of haunted Annapolis. Keep in mind that this doesn’t include drinks, so if you’re seeking a fully inclusive pub experience, you’ll need to budget accordingly. Yet, many reviewers find the quality of storytelling and the cozy pub atmospheres justify the expense.

Reviews highlight the guide’s expertise and friendly demeanor. One guest praised Ryan as a “terrific guide,” suggesting her storytelling made the experience especially enjoyable. Others appreciated the cozy pubs and the stories, although some wished for more ghost tales rather than the time spent in each bar.

Who Will Love This Tour?

This tour is ideal for travelers who enjoy historical stories with a supernatural twist. It’s perfect if you’re looking for an evening activity that combines a relaxed pub crawl with engaging storytelling. It suits groups of friends, couples, or solo travelers eager for a different way to experience Annapolis.

While not meant to be a highly intense or terrifying ghost hunt, it offers enough spooky flavor to satisfy those intrigued by spirits and haunted history. It’s also suitable for those who appreciate a casual social setting, especially since the tour emphasizes local pubs rather than a formal ghost-hunting expedition.

The Sum Up

The Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl provides a lively, authentic glimpse into the city’s haunted past, with stories backed by local lore and friendly guides. The cozy pubs, historical sites, and ghostly tales create a relaxed yet engaging atmosphere — perfect for an evening out that’s both fun and slightly eerie.

Whether you’re a history lover, a ghost enthusiast, or simply looking for a memorable night in Annapolis, this tour offers great value for its price and an experience that you’ll likely remember long after the drinks are gone. It’s best suited for those who enjoy storytelling, a bit of local color, and a relaxed social vibe, making it a charming way to spend an evening in Maryland’s charming capital.

FAQ

Is this tour suitable for children?
Most travelers can participate, but it’s best for older children or teenagers who enjoy ghost stories and are comfortable walking and standing for about two hours.

Are drinks included in the tour?
No, beverages are not included. You’ll want to bring extra cash if you wish to purchase drinks at the pubs.

How long does the tour last?
The tour is approximately 2 hours, starting at 6:00 pm, with stops at seven different locations.

Is the tour accessible for people with mobility issues?
It’s not recommended for those with mobility impairments due to walking and standing involved.

Where does the tour start and end?
It begins and ends at 22 Market Space in Annapolis, MD, making it convenient for those staying nearby.

Can I cancel the tour if my plans change?
Yes, free cancellation is available if done at least 24 hours in advance, allowing a full refund.

This tour offers a fun, atmospheric way to explore Annapolis’ haunted side while enjoying some of its historic pubs. Perfect for those seeking a relaxed evening filled with stories, spirits, and a touch of the supernatural.